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#$Date: 2022-11-12 03:50:58 +0200 (Sat, 12 Nov 2022) $
#$Revision: 279242 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/89/7158983.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158983
loop_
_publ_author_name
'Sobhani, Maryam'
'Figueira de Abreu, Rúben Manuel'
'Villinger, Alexander'
'Ehlers, Peter'
'Langer, Peter'
_publ_section_title
;
 Synthesis of imidazo[1,2-a]benzoazepines by alkyne-carbonyl-metathesis
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB01320G
_journal_year                    2022
_chemical_formula_moiety         'C20 H16 N2 O'
_chemical_formula_sum            'C20 H16 N2 O'
_chemical_formula_weight         300.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2022-04-06 deposited with the CCDC.	2022-11-09 downloaded from the CCDC.
;
_cell_angle_alpha                96.896(6)
_cell_angle_beta                 102.772(5)
_cell_angle_gamma                106.607(5)
_cell_formula_units_Z            2
_cell_length_a                   7.6764(15)
_cell_length_b                   10.420(2)
_cell_length_c                   10.633(2)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      35.08
_cell_measurement_theta_min      2.59
_cell_volume                     779.4(3)
_computing_cell_refinement       'Bruker Apex V7.51A'
_computing_data_collection       'Bruker Apex V7.51A'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            34631
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.499
_diffrn_reflns_theta_min         2.955
_diffrn_source                   'microfocus sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.7204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.478
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         5636
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0419
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0718P)²+0.1675P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1176
_refine_ls_wR_factor_ref         0.1235
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4989
_reflns_number_total             5636
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob01320g2.cif
_cod_data_source_block           is_rfmyca32
_cod_database_code               7158983
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.971
_shelx_estimated_absorpt_t_max   0.992
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.44311(11) 0.79009(7) 0.01771(7) 0.03050(15) Uani 1 1 d . . . . .
N1 N 0.48149(8) 0.57712(6) 0.17357(6) 0.01524(12) Uani 1 1 d . . . . .
N2 N 0.77040(9) 0.62322(7) 0.14345(7) 0.02195(14) Uani 1 1 d . . . . .
C1 C 0.58256(13) 0.75487(9) 0.04080(9) 0.02648(17) Uani 1 1 d . . . . .
H1 H 0.6826 0.7978 0.0055 0.032 Uiso 1 1 calc R U . . .
C2 C 0.60963(11) 0.65268(8) 0.11776(7) 0.01851(14) Uani 1 1 d . . . . .
C3 C 0.74356(11) 0.52598(9) 0.21802(8) 0.02113(15) Uani 1 1 d . . . . .
H3 H 0.8342 0.4842 0.2516 0.025 Uiso 1 1 calc R U . . .
C4 C 0.56626(10) 0.49655(8) 0.23803(7) 0.01885(14) Uani 1 1 d . . . . .
H4 H 0.5136 0.4326 0.2871 0.023 Uiso 1 1 calc R U . . .
C5 C 0.28826(10) 0.58031(8) 0.16484(7) 0.01808(13) Uani 1 1 d . . . . .
H5A H 0.2204 0.5696 0.0715 0.022 Uiso 1 1 calc R U . . .
H5B H 0.2943 0.6699 0.2124 0.022 Uiso 1 1 calc R U . . .
C6 C 0.18159(10) 0.46844(7) 0.22274(7) 0.01619(13) Uani 1 1 d . . . . .
C7 C 0.19907(10) 0.48607(7) 0.35912(7) 0.01563(13) Uani 1 1 d . . . . .
C8 C 0.09664(11) 0.38020(8) 0.40963(8) 0.02011(14) Uani 1 1 d . . . . .
H8 H 0.1074 0.3917 0.5013 0.024 Uiso 1 1 calc R U . . .
C9 C -0.02056(12) 0.25850(8) 0.32645(9) 0.02499(16) Uani 1 1 d . . . . .
H9 H -0.0899 0.1871 0.3614 0.030 Uiso 1 1 calc R U . . .
C10 C -0.03697(12) 0.24060(9) 0.19221(9) 0.02612(17) Uani 1 1 d . . . . .
H10 H -0.1168 0.1570 0.1356 0.031 Uiso 1 1 calc R U . . .
C11 C 0.06368(11) 0.34530(8) 0.14111(8) 0.02146(15) Uani 1 1 d . . . . .
H11 H 0.0520 0.3328 0.0493 0.026 Uiso 1 1 calc R U . . .
C12 C 0.32109(10) 0.61062(8) 0.44566(7) 0.01719(13) Uani 1 1 d . . . . .
C13 C 0.42644(10) 0.71499(7) 0.51840(7) 0.01761(13) Uani 1 1 d . . . . .
C14 C 0.55573(10) 0.83798(7) 0.60390(7) 0.01767(13) Uani 1 1 d . . . . .
C15 C 0.68905(11) 0.92777(8) 0.55624(8) 0.02070(14) Uani 1 1 d . . . . .
C16 C 0.81282(12) 1.04655(8) 0.64261(10) 0.02734(18) Uani 1 1 d . . . . .
H16 H 0.9029 1.1090 0.6119 0.033 Uiso 1 1 calc R U . . .
C17 C 0.80745(13) 1.07564(9) 0.77234(10) 0.02986(19) Uani 1 1 d . . . . .
H17 H 0.8944 1.1567 0.8294 0.036 Uiso 1 1 calc R U . . .
C18 C 0.67530(14) 0.98654(9) 0.81875(9) 0.02755(17) Uani 1 1 d . . . . .
H18 H 0.6711 1.0065 0.9074 0.033 Uiso 1 1 calc R U . . .
C19 C 0.54922(12) 0.86804(8) 0.73469(8) 0.02179(15) Uani 1 1 d . . . . .
H19 H 0.4581 0.8070 0.7659 0.026 Uiso 1 1 calc R U . . .
C20 C 0.69529(13) 0.89490(9) 0.41621(9) 0.02746(17) Uani 1 1 d . . . . .
H20A H 0.5777 0.8948 0.3569 0.041 Uiso 1 1 calc R U . . .
H20B H 0.7101 0.8046 0.3988 0.041 Uiso 1 1 calc R U . . .
H20C H 0.8022 0.9638 0.4015 0.041 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C2 106.44(6) . . ?
C4 N1 C5 126.44(6) . . ?
C2 N1 C5 127.11(6) . . ?
C2 N2 C3 105.08(6) . . ?
O1 C1 C2 125.57(8) . . ?
O1 C1 H1 117.2 . . ?
C2 C1 H1 117.2 . . ?
N2 C2 N1 111.69(7) . . ?
N2 C2 C1 122.13(7) . . ?
N1 C2 C1 126.17(7) . . ?
N2 C3 C4 110.37(7) . . ?
N2 C3 H3 124.8 . . ?
C4 C3 H3 124.8 . . ?
N1 C4 C3 106.42(7) . . ?
N1 C4 H4 126.8 . . ?
C3 C4 H4 126.8 . . ?
N1 C5 C6 111.20(6) . . ?
N1 C5 H5A 109.4 . . ?
C6 C5 H5A 109.4 . . ?
N1 C5 H5B 109.4 . . ?
C6 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C11 C6 C7 119.26(7) . . ?
C11 C6 C5 119.79(7) . . ?
C7 C6 C5 120.95(6) . . ?
C8 C7 C6 119.46(7) . . ?
C8 C7 C12 119.99(6) . . ?
C6 C7 C12 120.55(6) . . ?
C9 C8 C7 120.32(7) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.30(7) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 119.79(7) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C6 120.87(7) . . ?
C10 C11 H11 119.6 . . ?
C6 C11 H11 119.6 . . ?
C13 C12 C7 178.94(8) . . ?
C12 C13 C14 178.44(8) . . ?
C19 C14 C15 120.41(7) . . ?
C19 C14 C13 119.93(7) . . ?
C15 C14 C13 119.65(7) . . ?
C16 C15 C14 117.97(8) . . ?
C16 C15 C20 121.91(8) . . ?
C14 C15 C20 120.12(7) . . ?
C17 C16 C15 121.60(8) . . ?
C17 C16 H16 119.2 . . ?
C15 C16 H16 119.2 . . ?
C18 C17 C16 120.13(8) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 119.54(8) . . ?
C17 C18 H18 120.2 . . ?
C19 C18 H18 120.2 . . ?
C18 C19 C14 120.35(8) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C15 C20 H20A 109.5 . . ?
C15 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C15 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2128(12) . ?
N1 C4 1.3606(9) . ?
N1 C2 1.3664(9) . ?
N1 C5 1.4758(10) . ?
N2 C2 1.3341(10) . ?
N2 C3 1.3578(11) . ?
C1 C2 1.4516(11) . ?
C1 H1 0.9500 . ?
C3 C4 1.3772(11) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C5 C6 1.5026(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C11 1.3930(10) . ?
C6 C7 1.4109(10) . ?
C7 C8 1.3988(10) . ?
C7 C12 1.4303(10) . ?
C8 C9 1.3880(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.3896(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.3887(12) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.2056(10) . ?
C13 C14 1.4312(10) . ?
C14 C19 1.4035(11) . ?
C14 C15 1.4054(11) . ?
C15 C16 1.3954(11) . ?
C15 C20 1.5017(12) . ?
C16 C17 1.3886(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.3884(14) . ?
C17 H17 0.9500 . ?
C18 C19 1.3892(11) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N2 C2 N1 -0.05(9) . . . . ?
C3 N2 C2 C1 179.18(7) . . . . ?
C4 N1 C2 N2 0.26(8) . . . . ?
C5 N1 C2 N2 -179.05(6) . . . . ?
C4 N1 C2 C1 -178.93(8) . . . . ?
C5 N1 C2 C1 1.76(12) . . . . ?
O1 C1 C2 N2 -177.23(8) . . . . ?
O1 C1 C2 N1 1.89(14) . . . . ?
C2 N2 C3 C4 -0.18(9) . . . . ?
C2 N1 C4 C3 -0.36(8) . . . . ?
C5 N1 C4 C3 178.96(7) . . . . ?
N2 C3 C4 N1 0.34(9) . . . . ?
C4 N1 C5 C6 -7.36(10) . . . . ?
C2 N1 C5 C6 171.82(7) . . . . ?
N1 C5 C6 C11 -95.58(8) . . . . ?
N1 C5 C6 C7 84.36(8) . . . . ?
C11 C6 C7 C8 -0.54(11) . . . . ?
C5 C6 C7 C8 179.52(7) . . . . ?
C11 C6 C7 C12 179.11(7) . . . . ?
C5 C6 C7 C12 -0.83(10) . . . . ?
C6 C7 C8 C9 0.32(11) . . . . ?
C12 C7 C8 C9 -179.33(7) . . . . ?
C7 C8 C9 C10 0.12(13) . . . . ?
C8 C9 C10 C11 -0.34(13) . . . . ?
C9 C10 C11 C6 0.12(13) . . . . ?
C7 C6 C11 C10 0.33(11) . . . . ?
C5 C6 C11 C10 -179.73(7) . . . . ?
C19 C14 C15 C16 -0.15(11) . . . . ?
C13 C14 C15 C16 -179.93(7) . . . . ?
C19 C14 C15 C20 179.96(8) . . . . ?
C13 C14 C15 C20 0.18(11) . . . . ?
C14 C15 C16 C17 0.75(12) . . . . ?
C20 C15 C16 C17 -179.36(8) . . . . ?
C15 C16 C17 C18 -0.81(14) . . . . ?
C16 C17 C18 C19 0.25(13) . . . . ?
C17 C18 C19 C14 0.34(13) . . . . ?
C15 C14 C19 C18 -0.39(12) . . . . ?
C13 C14 C19 C18 179.39(7) . . . . ?
